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Responsive planning

Two things are true about me: I am extraordinarily undisciplined, but I manage to get a tremendous amount of productive work done.

I don’t know if I’m just wired up weirdly, or whether it’s a case of “there’s more than one way to do it”–but the idea of writing up a detailed plan and then sticking to it is the stuff of nightmares to me. I write plans constantly, but they’re more like an exercise in creative brainstorming than any sort of promised course of action.

But I said I get a lot of productive work done, right? How is that possible without sticking to well thought out plans? Well, that part I’ve figured out: if you can’t be (locally) predictable, then you need to be globally flexible.

What do I mean by flexibility? I mean keeping a schedule that by default is completely and utterly open. So when you look at a 12 week slice of my life, there may be a handful of deadlines, meetings, and other responsibilities sprinkled in, but 90% of my time is a blank canvas–which I can fill in with whatever I want.

Of course, that’s a bit misleading without some added context. My workload and my list of “things I owe other people” is massive, mostly because of commitments made years ago that haven’t fully cleared my system since I switched to this new way of working about a year ago. And so there are always dozens of different things competing for my attention, even after I weed out all the “nice to have” and “interesting but non-essential” responsibilities.

So how do I keep track of all of those things? Do I use some huge “Getting Things Done” system in which I have a comprehensive list of everything I need to do for everything and then just churn away at whatever catches my eye whenever I have time to work? No.

Instead, I use theming to guide my work. I whitelist a handful of core activities (I.e. working on my book, training my apprentice, etc.) and then give myself full permission to spend as much time as I want on those activities. I only allow myself a handful of these themes at any point in time (Ideally 2-3, no more than 5)–and these then become my primary measure of progress for as long as I chose to focus on them.

But having themes does not mean focusing with laser-like precision on these tasks and these tasks only. It only means that if I were to summarize my work over the period of a few days or a few weeks, those themes ought to be visible in my output, and stand out against the background (AKA “Everything else I do”) — 60% on theme work is just fine, 30% is a criminal lack of focus.

For the “everything else” side of the equation, I treat it like a flow. I keep a big stack of unlined index cards nearby at all time, and when an idea comes up or I’m reminded of some responsibility, I write down notes on individual cards that just pile up on my desk. I try to scope them to actionable, deliverable tasks, but sometimes they are just vague notes that are meant to serve as reminders that will later be turned into several more specific cards. Several times a day (when I’ve got a bit of downtime, or when I’m tired of working “on theme”) I shuffle through this deck, reordering it based on what essentially amounts to gut feelings combined with new information combined with a rough simulation of what my schedule might look like over the next few days.

When that pile gets huge (and sometimes it does), it’s a signal to me that I need to either set aside time to burn through some of the stuff that has been piling up, decide to declare bankruptcy on some of the tasks/projects, or most radically, switch up my themes so that whatever is generating the lionshare of all these “Everything else” cards becomes my main area of focus for a while.

This is an idealization of what I actually do. But I think it’s pretty close.